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The Most Stylish Way to Celebrate Career Milestones? Hint: Diamonds Are Involved

It’s seriously refreshing to hear that someone like Hillary Kerr—our co-founder, chief content officer, and resident Vanderpump Rules expert—can appreciate how easy it is to get bogged down with the whirlwind of the day-to-day. And given that she built WWW from the ground up, co-wrote three books, launched not one but three lines at Target, and recently found just a little spare time to host a wildly successful podcast (3MM+ downloads and counting) and become mom to a handsome young gentleman by the name of Clark, it’s fair to say she’s uniquely qualified to dish out career advice…

She’ll start by telling you to pause and really celebrate the wins that make all this hard work so worth it. When I asked how she treats herself to mark important moments (without defaulting to buys that only end up in the back of her closet), Hillary gave me an unexpected (but very appealing) answer: precious, one-of-a-kind natural diamonds with fascinating backstories. Keep reading for the inside intel from one wickedly smart, wickedly funny boss—and spy some natural diamond jewelry that’s positively ripe for self-gifting, inspired by Hillary’s own pieces (including those chic little earrings she flat-out refuses to take off).

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Who What Wear

First off, we know what your job entails, but how would you describe what you do for a living to someone who doesn’t know the industry?

I’m the chief content officer for Who What Wear, which means I oversee our editorial, social, creative, and copy teams here in the U.S. and the UK. I also host and produce my podcast, Second Life, which I created a year ago for the company. I think my job is pretty straightforward; if you look at or read anything we create, I have a hand in it!

Can you tell us about some significant milestones you’re most proud of?

Well, to be frank, most of my career has been spent at Who What Wear, so that’s where my most memorable achievements have happened. Writing three books is definitely at the top of that list, as is our inclusive collection at Target. I’m also really proud of what we’ve built with Second Life; it’s truly the most fun thing to work on, and it seems to really resonate with our audience too. But the biggest thing that I’m proud of is creating this company with Katherine Power. When we started the company in 2006, no one thought we’d make it. I’m so proud that nearly 13 years later, we’re still flourishing and have built the most amazing team. 

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Who What Wear

What’s the first meaningful purchase you ever remember treating yourself to?

It took me a long time to actually invest in myself. The first time I remember doing something noteworthy was buying a dress from Jason Wu’s S/S 11 collection, which I wore to the L.A. dinner party we threw to celebrate our second book, What to Wear, Where. It was the first time I’d ever bought a dress from a runway collection, and it was certainly the most expensive purchase I’d ever made.

The dress is perfect, and I still love it to pieces, but now I prefer buying myself natural diamonds, in part because of the price-per-wear aspect. No matter how much you love a dress, there’s only so much you’re going to wear it. But diamonds… Well, you can wear them every single day, and they only make you happier. Plus they’re seasonless and a great investment—what’s not to love?

What is it about natural diamonds in particular that really speaks to you?

I love their backstory. Diamonds are billions of years old, they’re truly individuals—every single diamond that exists on this planet is totally one-of-a-kind, and took eons to create under really crazy and intense condition. I think that’s magical, and that makes them my favorite gemstone by far.

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Who What Wear

How would you describe your work wardrobe? Is there anything you wear every single day or put on especially when you want to feel confident?

A strong blazer is always a key piece of my work wardrobe, as it can make me feel pulled together, even when I’m having a rough day. I also always wear a handful of pieces of jewelry; my mismatched diamond lightning-bolt and evil-eye earrings are crucial for me. I literally never take them off.

Tell us more about that!

I’m a little funny about the earrings; the evil eye was a gift from my mother, and the lightning bolt I bought myself after my son was born. The combo makes me feel protected, in some cosmic way.

We love that idea of self-gifting…

No one needs to give you permission to celebrate yourself and your achievements, and that’s why I think it’s important to take a moment and recognize that you did something incredible. That feels so empowering and satisfying to me.

Do you have any other jewelry pieces you wear on a regular basis?

My diamond engagement ring is a family heirloom—the center stone is an old-mine diamond that was cut in the late 1800s, while the four emerald-cut baguettes on either side were actually cut in the early 1950s, all set in platinum—and I wanted to leave the setting exactly the same because it’s perfect the way it is. Regarding our wedding bands, we worked with our amazing jeweler to source vintage diamonds from the same era as the center stone of my engagement ring. Our reasoning was this: Even though the diamonds were new to us, they were cut at the same time my engagement ring was created, in the late 1800s, and we thought that honored the past in a really sweet way. We loved that the wedding bands are both old and new, and something that my husband and I designed together.

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Who What Wear

How does your day-to-day differ from what people assume? What’s a common misconception you hear on repeat?

I don’t think people realize that I’m as hands-on when it comes to our content. Yes, I deal with high-level strategy every day, but I’m also in brainstorms and editorial meetings every single day, too. I also love working with our incredible sales team and enjoy that piece of my work tremendously. Most people don’t realize I do all the booking, questions, and research for the Second Life podcast, but I do!

Is your current career path the one you envisioned for yourself when you were growing up?

I had a lot of ideas about what I wanted to be when I grew up, and frankly this is both better than what I ever imagined for myself, and totally on brand. I always knew I’d work with words in some way or another, but I never thought I’d be an entrepreneur.

What was a weird challenge you faced as you built Who What Wear that people don’t really know about?

Now everyone loves the digital space, but back when we started the company, no one in fashion, beauty, or entertainment wanted anything to do with it. So I think the fact that we had to educate people on what digital and social even looked like was definitely a challenge.

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Who What Wear

Do you feel like a success? What was your picture of a “successful woman” when you were younger?

Yes and no. In many ways, I’m so proud of what we’ve accomplished, but I also see that there’s so much left to do, and that excites me. In my head, a “successful woman” wore suits and heels and went to an office every day. I’m not much for suits, but I do love heels—and my office.

We’ve noticed you seem to wear your diamond necklaces every day as well… Can you tell us about that? 

I think my personal style runs on the feminine side, but I also love strong moments and vintage pieces too, and that really explains my collection of jewelry as well.

We know you’re in hot demand and do these kind of interviews a lot! What do you wish people would actually ask?

I’m a bit of a pop culture nerd, and I really wish someone would ask me about my thoughts on Vanderpump Rules (which is essential viewing, in my opinion), Killing Eve (I’m obsessed), or the ice cream recipes I’ve been testing for #GameOfCones, which is my ice cream side hustle to go with the show.

Let’s finish things up with a few rapid-fire questions!

Gold or silver? Gold.

Your favorite diamond shape? Emerald.

Vintage or custom? Vintage.

Minimalist or do you “excessorize”? More is more.

Ankle jewelry: yay or nay? Yay, but also not for me.